Ammonium Hydroxide → HCID 71248874, compound

HRID 1519089Notes

Reaction equation

HRID 1519089 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1([C:18]([NH:20][CH:21]2[CH:28]3[CH2:29][C:24]4([C:31]([OH:33])=O)[CH2:25][CH:26]([CH2:30][CH:22]2[CH2:23]4)[CH2:27]3)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:10])=[O:9].Cl.C([N:37]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[NH4+].[OH-]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1([C:18]([NH:20][CH:21]2[CH:22]3[CH2:23][C:24]4([C:31]([NH2:37])=[O:33])[CH2:25][CH:26]([CH2:27][CH:28]2[CH2:29]4)[CH2:30]3)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:9])=[O:10]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71246296HCID 71246296, compound

Product 1

HCID 71248874HCID 71248874, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 25-mL flask, 4-{[1-(2-bromo-benzenesulfonylamino)-cyclohexanecarbonyl]-amino}-adamantane-1-carboxylic acid (106 mg, 0.196 mmol) and methylenechloride (20 mL) were charged, and then sequentially 1-ethyl-3-(3-dimethylaminopropyl)carbodiimidehydrochloride (76 mg, 0.392 mmol) and 1-hydroxybenzotriazol (54 mg, 0.392 mmol) were added thereto, followed by stirring for 5 minutes at room temperature. The resultant solution was added with 35% ammonia aqueous solution (1.1 mL), followed by stirring for 12 hours at room temperature. After the reaction was completed, purified water (10 mL) was added thereto, and the aqueous solution layer was washed with methylenechloride (30 mL) twice. The obtained organic layer was added with magnesium sulfate so as to remove remaining moisture. Through filtering and vacuum evaporation, the residue was obtained. The mixture was purified with column chromatography (MC/MeOH=20:1) so as to obtain 4-{[1-(2-bromo-benzenesulfonylamino)-cyclohexanecarbonyl]-amino}-adamantane-1-carboxylic acid amide (62 mg, 59%).

Workup

  1. stirringby stirring for 12 hours at room temperature
  2. custompurified water (10 mL)
  3. additionwas added
  4. washthe aqueous solution layer was washed with methylenechloride (30 mL) twice
  5. additionThe obtained organic layer was added with magnesium sulfate so as
  6. customto remove
  7. filtrationThrough filtering
  8. customvacuum evaporation
  9. customthe residue was obtained
  10. customThe mixture was purified with column chromatography (MC/MeOH=20:1) so as

Sources & evidence

ORD record
ord-9aa1a20718724dc5a48846afc4f4303a
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

Loading…